In 1907, Jackson and Orage bought The New Age, a struggling Christian Socialist weekly magazine, with financing from Lewis Wallace and George Bernard Shaw.

At the same period he set up in 1912 or 1913 the Flying Fame Press, with the poet Ralph Hodgson and designer Claud Lovat Fraser.

[3] This was the beginning of a long association with small press and the worlds of typography and book collecting, on which he wrote extensively.

He was in the short-lived Fleuron Society (1923) with Stanley Morison, Francis Meynell, Bernard Newdigate and Oliver Simon.

After World War I, Jackson introduced Orage to C. H. Douglas, who subsequently wrote economics articles for The New Age, expounding his theory of Social Credit.